Musings + Essays

Are You Good at Negotiating?

By: Jen Shoop

Do you negotiate? Are you good at it? I have a good friend in commercial real estate who practically salivates over the opportunity to negotiate. He bought a parking spot beneath his building here in Manhattan a few years ago and I remember him intoning: “It was the best, most exciting deal I’ve ever done.” (Clearly, he’s chosen the correct profession.) I can’t say I share in his thrill with negotiating, but Mr. Magpie and I have been through countless negotiations together, both as business owners and determined administrators of our home life together, and I have gradually worked my way from a place of dreading them to viewing them as a necessary evil to re-interpreting them as an occasion to advocate for myself.

When I was younger, I tended to assume the answer was always “no,” and would talk myself out of negotiating before the conversation had even started. (I would later learn this to be a chief tactic amongst seasoned negotiators: get the other party to negotiate with itself — usually by refusing to make the first offer — and you don’t need to do as much work.) I was particularly this way about formally-presented offers, i.e., “We are pleased to offer you this position with a starting salary of x” or “Your application for this apartment has been approved; the rent will be $x.” The declarative structure of these “invitations” made me feel as though everything was a done deal and that I would be out of line to ask for anything different. (Once a rule follower, always a rule follower…) I now understand that everything is a posture — including the formal language! — and that there is very little that isn’t negotiable. With intensive coaching from Mr. Magpie, who has reminded me on countless occasions that “you miss every shot you don’t take” and “if you don’t ask, the answer is always ‘no,'” I have gotten more comfortable with countering. At the beginning, I was often worried that countering would make me unlikeable or would hurt someone’s feelings, but those assumptions have proven either incorrect or unfair to myself — or both. The key for me has been realizing that I don’t need to be rude or unpleasant to negotiate. I can present an alternative calmly and politely in a way that gestures toward fairness for all parties. I typically start my counter offers by saying: “Thank you so much for the generous offer” or “I’m honored by this opportunity…” or “This is such exciting news!” A small thing, but starting the conversation from a place of gratitude and acknowledgement helps me put my best foot forward and tends to build goodwill.

Nowadays, my biggest stumbling block in the negotiations arena is the old “bird in the hand” mindset I occupy in all realms of my life — that is, “a bird in the hand is better than two in the bush.” I can’t tell whether this mentality is a condition of expediency or risk intolerance. Mr. Magpie will go through multiple rounds of counter-offers to get to a place that he deems fair. Meanwhile, I would rather have a firm resolution that’s in the ballpark of what I want than sit uncomfortably in limbo going back and forth and worry that I’ve risked the entire enchilada. Mr. Magpie often makes the valid point that it is pretty rare an entire deal will go asunder by adding an extra round of negotiation — most of the time, both parties are pot-committed and determined to make things work by that point. This has proven to be correct over time, but doesn’t make the experience any less of a nail-biter for me.

Mr. Magpie and I have been in a number of these kinds of negotiations recently in the process of buying our new home, finding movers, renting our current apartment in NYC, selling various items in our home, etc, and I’m always a bundle of nerves, begging him not to go back again, while he displays flinty determination in getting to a satisfactory result. I should note that he is never untoward or unpleasant in these conversations. He is calm, collected, rational, gentlemanly. Still, I find the process gut-turning. On my run the other morning, I found myself wondering whether the delta between us in this regard is a gender thing, a personality thing, or the result of his MBA? (Probably a combination of all three?) One framework he shared the other week that has helped me better accommodate his perspective involved acknowledging and identifying constraints on both sides of the negotiation. That is, it often feels as though I have the most to lose in a negotiation, but that’s not necessarily true. As an example, I have worked with various vendors over the years. It has felt at times as though I will run the risk of entirely losing the opportunity to work together if I don’t accept the proposed terms, my constraints being budget and ability (I actually cannot do that thing by myself). However, the vendor is operating under its own constraints, and it is worthwhile to take a minute to imagine what they might be. As an example, it probably cost the vendor a lot of time and money (whether marketing, staff time, etc) to acquire me as a customer, and it is less expensive for them to drop the price on my project than it is to find a new lead and bring her to the point of contract.

My broad point here is that negotiating is a skill developed over time, and it is worthy of practice. Running two businesses has taught me that no one will advocate for you. You must be willing to advance your own objectives or someone else’s will supersede your own. (Sometimes, by the way, that’s OK — there are issues that are not particularly important, or costly, or worth your time, or maybe you just think the other party deserves it. But sometimes, it is a matter of fairness, and sometimes you are being taken for a ride. I have been!) I should add that these principles do not only apply to my narrow experiences with entrepreneurship. Some of the best negotiators I know are stay-at-home mothers who know how to navigate healthcare systems with sophistication, get a fair deal on home services, achieve a better outcome with customer service representatives, etc. You have to show up for yourself — no one else will!

What about you? How do you approach negotiation? Are you good at it?

Related to this post: how risk tolerant are you?

Shopping Break.

+Super elegant dress (on sale for $124!) for something like a Baptism, baby shower, luncheon, etc.

+This $50 marble footed fruit bowl is so elegant! Would be a great way to display fruit/citrus on a counter. Also a fun house-warming gift!

+Love this linen maxi for a barefoot backyard BBQ. Would work with bump!

+Into the look of layered gold pendants — this set is $110 and so chic, and Shashi also has some fun and reasonably priced styles if you want to create your own set.

+Speaking of, I feel as though I’ve worn statement earrings for years now but completely neglected statement necklaces. This Roxanne Assoulin and this Lizzie Fortunato are helping me course-correct.

+This cherry print one piece is in my cart — 50% off!

+Drooling over these sandals.

+OMG this custom peg doll family! Sweet gift for a new big sister.

+This cute blue botanical dress for a little lady was just discounted — you can twin with your little one wearing this matching mama style.

+These shoes are SO chic! I know a lot of you are fans of this brand. I think they’d be a great summer alternative to my velvet Birdie mules I wore all winter long!

+Gingham midi dress in an on-trend shape (Sleeper vibes) for under $30.

+They are an investment, but these Minnow rash guards are just the best. They fit snugly and the blue color goes with so many of the suits I tend to buy. Plus, gender neutral so can be passed down from sibling to sibling!

+Did you know Free People sells activewear? These $30 shorts are a bestseller and come in fantastic colors.

+Adore this floral blouse.

+Cute side table for outdoors.

+Speaking of outdoors: PSA — S&L has marked down their outdoor furniture through July 6. A few of their tables have been contenders in my current search for patio dining furniture and this promo might push me over the edge. This this teak garden table (I like that the white legs open up fun possibilities for contrasting chairs) is towards the top of my list.

+Such a pretty pillow — would be great for pattern/color mixing. (More chic throw pillows here.)

+European pharmacy beauty favorites.

+Lake Pajamas keeps coming with the hits — I am in love with their new caftan! Hoping they release it in even more colors.

+Now THIS dress is ready to party.

+More clothes to celebrate in.

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14 thoughts on “Are You Good at Negotiating?

  1. I heard a great comment to think of salary negotiations as making a lot of money to be uncomfortable for a few hours. I do wonder if women are judged more harshly for negotiating at work and life than men?

    I do want to recommend this resource – I went to a free workshop, which was worth my time. There is a free online course AAUW (American Association of University Women) Work Smart and Start Smart Salary Negotiation:

    1. Thank you for the link, and also for this perspective — “a lot of money to be uncomfortable for a few hours.” So true!!


  2. Wow. This is a post that everyone (especially every woman) should read. I recently started a new job and knew that negotiating is always important. Despite experience attempting salary negotiations, I still wasn’t fully confident. I hired a consultant to help negotiate- she helped with research, crafting my dialogue with rational and reasoning for each ask. I looked at hiring her as similar to hiring someone to help craft a better resume. She assured me that I am worth it and was doing the right thing. Her business focuses on helping women and underrepresented people get paid fairly and I highly recommend it.

    I’ve been fairly good at negotiating little things like a better hotel room, restaurant table, etc. Learning to advocate for myself in bigger situations is a lifelong process but I am happy with the progress I’ve made.

    1. Wow! Good on you, Melinda! I didn’t even know this was a service that existed, and so glad you thought to find the support you needed! Cheers to you, and thanks for sharing this. Maybe there are some other Magpies who will benefit from learning about this option, too!


  3. Before my oldest was born, I worked in purchasing for many years…and I still hate negotiating! Although I do find myself recognizing opportunities for others to negotiate and encouraging them to do so. It’s still hard for me to even think to push back on some purchases, since so many everyday items (groceries, clothing, big box stores, etc) are fixed prices. That makes it easy to forget that a price quoted for a service or large item for the home can be negotiated. I think it is key to have multiple options, though, so you can go in with more of a “nothing to lose” mindset. That was part of the issue in my old job…due to industry consolidation, often there was no other company that could supply what we needed to all our manufacturing locations across the country. So if our vendor said, “there’s going to be a price increase,” we could push back a bit, but in the end we were stuck with them. Thank goodness that’s not the case with the things I’m buying these days (looking at you, new basement carpet)!

    1. Hi Stephanie! Thanks for chiming in here, and especially for noting that there ARE circumstances where negotiation just can’t or won’t work, or isn’t appropriate, or isn’t worth the time/energy for the incremental gain. I always assess the expediency factor in particular — “is going back and forth over email for a week worth it?” Sometimes, yes, out of principle. Other times, not at all, especially when the time it will take me to achieve the outcome is not worth the actual outcome. (i.e., My time is more valuable than spending an hour going back and forth to save $10.) I also personally feel like there is a threshold (very difficult to define) where you lose credibility a bit if you keep going back for more/appear to be splitting hairs/can’t come to a consensus after many back and forths. This is so hard to pin down, but I do feel like you need to take that into account, especially when negotiating with an employer, whom you will be working with for a long time. You want to seem confident in your abilities and your worth, but you don’t want to seem like you will be difficult to work with. This doesn’t mean you can’t go through multiple rounds of negotiation, but there is definitely an art and it takes some EQ to figure out where to draw the line. I think, as someone else noted, women tend to draw the line earlier than men, but anyway — there are lots of shades of gray in this entire area!

      So much to think about.


  4. This is interesting! As a fellow rule-follower, I too have felt like negotiations were beyond me at times … but over the years I’ve gotten better at it, and salary negotiations have been such a great (if totally nerve-wracking) training ground for me. I have found it totally empowering to ask for what I know I deserve and then (hopefully) achieve it or come closer to it. It’s such a rush! I would be interested in reading more about the gender/sex aspect of negotiations. Also, I wish I had my MBA. haha!


    1. Me too, MK! I find Landon applying it to so many different realms. It’s also come in personal handy for me — I would have been lost on how to create a balance sheet or P&L statement…

      Good on you for persisting in the salary negotiations. I think the hardest one is the first. Then you learn and you realize you’re not doing anything wrong and you get better at it with time.


  5. Great question. As someone in a career focused on the arc of short and long term negotiating (government relations/lobbyist), I have become more comfortable with age on this. It doesn’t always come naturally (fellow rule-follower, too!), but I tend to find myself naturally advocating for things more in personal and social settings, e.g. for my friends, groups, etc. when we go out …. “actually, this table all the way in the back corner near the restrooms doesn’t work for us – could we look for another spot? thanks so much!” or, a recent real-life example “oh, the wait will be much longer, despite our reservation? i wonder if we could enjoy a complimentary glass of something while we wait…”. Similarly, with the dozens of contractors we’ve engaged with over the past two years of historical-home ownership, I’ve become *very* comfortable being forthcoming and direct in negotiating price, timeline, etc.

    Salary-esque stuff still feels uncomfortable & I definitely want to practice flexing that type of negotiating muscle more. I tend to find my best power is in a deliberate silence; often, the less said, the better – and the other person is quick to jump to fill the silence and rapidly offer something/progress the discussion to fill the gap.

    I’d love to hear what others say on this, especially from the comradery of a female lens. Though not always the case, I find myself self-limiting in the sense of internal “am I being too harsh? will they judge me? did i speak out of turn? do i seem to junior/inexperienced to be asking this? am i too much? should i have let my male boss speak first?” etc., generally in professional settings.

    Definite food for thought!

    1. Hi Erica! Can we be friends IRL? I love a friend who isn’t afraid to ask for better accommodations! I have a close girlfriend who is exactly like this, and she is SO good at having a light touch about it, too. I don’t know how she does it, but somehow she always endears herself to the waiter/staff/etc and never seems pushy or demanding or anything like that. Major goals! I’ve gotten better about this with time, but she really takes it to a different level.

      I have been through the same litany of thoughts on how gender impacts my willingness/ability to negotiate. I especially find myself thinking: “did I speak out of turn?” and “did I turn that person off?” I think your point about deliberate silence is spot-on. It is SO hard not to yammer away and fill the void, but you often achieve better results by just zipping your lips and listening. In some cases, I use a mnemonic — I sit on my hands (if I’m on a call and not visible to the other party) as a reminder NOT TO SPEAK. I say my part, then sit on my hands and bite my tongue. It helps! Another seemingly silly adjacent move that has helped me in various ways — physically taking up more space in a room. Stretch out a bit, move your papers around, push your chair back, put your hands behind your head, etc. Sometimes physically taking up more space makes me feel more empowered in situations where I am negotiating, or nervous, or whatever.

      Lots to think about! Thanks for sharing!


    2. Umm yes x a million to being friends IRL! The dream!

      Love the tip about taking up space too. Even though I’m 5’9″ish, I love wearing heels to work, standing with my hands on my hips, etc. – never thought of this as a component to the subtle negotiation process, but it’s something I’ll definitely keep in mind now.

      Really enjoying reading these other comments too!

  6. This post really resonated with me. I am in the process of getting promoted (yay!) but also negotiating the salary and terms. It hasn’t been totally pleasant but I appreciate your comments here.

    I have read your blog for years now (also have kids similar in ages… nearly 4 and nearly 2) and whenever I see a new post from you I think – wow, this is perfect timing / aligns with what I am looking for or thinking… so thanks for that 🙂

    1. Hi Meghan! I absolutely love hearing from long-time readers, first-time commenters — thank you for taking the time to leave this note, and for your continued readership. I’m so glad we are on the same page! Congratulations on the promotion, and sending you BIG 2021 VIBES as you make your way through this negotiation (that is: all things auspicious). It is so nerve-wracking to negotiate around salary/position. I often felt as though I was overstepping my bounds / being “too greedy” by asking for more than was initially offered. But I am so glad I did. In two separate instances, I managed to negotiate a significantly higher salary just by countering once. Worth the heartburn. Will be thinking of you and cheering you on!!


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